10H-spiro[acridine-9,9'-xanthene] Chemical Properties

Boiling point:

497.2±45.0 °C(Predicted)

Density 

1.33±0.1 g/cm3(Predicted)

pka

1.11±0.20(Predicted)

InChI

InChI=1S/C25H17NO/c1-5-13-21-17(9-1)25(18-10-2-6-14-22(18)26-21)19-11-3-7-15-23(19)27-24-16-8-4-12-20(24)25/h1-16,26H

InChIKey

LRDZIHIBFOPYFK-UHFFFAOYSA-N

SMILES

C1=C2C(NC3=C(C42C2=C(C=CC=C2)OC2=C4C=CC=C2)C=CC=C3)=CC=C1

10H-spiro[acridine-9,9'-xanthene] Usage And Synthesis

Description

10H-spiro[acridine-9,9'-xanthene] is a weak electron donor moiety. Its structure is similar to spiro[acridine-9,90 -fluorene] and their properties are similar. They all have effective donor properties and the expectation of a large dihedral angle arising from steric repulsion by the two H atoms in the peri-position. Hence, they are often used simultaneously to synthesize TADF and compare the properties of the two synthesized materials.

Uses

10H-spiro[acridine-9,9'-xanthene] could used as an intermediates of photoelectric materials to fabricate a TADF OLED emitter. Since its good donor properties and the expectation of a large dihedral angle arising from steric repulsion by the two H atoms in the peri-position, it was commonly selected as a wide-gap donor moiety to fabricate highly efficient blue TADF materials whit diphenylsulphone (DPS) as an electron acceptor[1]. 10H-spiro[acridine-9,9'-xanthene] is also used to construct phosphine oxide (PO) hosts through introducing one or two diphenylphosphine oxide groups at 2 and 7 positions of acridine ring, respectively. This material could used to fabricate single-emissive-layer Thermally activated delayed fluorescence (TADF) white organic light-emitting diodes[2].

References

[1]Lee G R, et al. Theoretical Study of Benzofuro-Pyridine Derivatives-Based Organic Light-Emitting Diodes Exhibiting Thermally Activated Delayed Fluorescence. Journal of Nanoscience and Nanotechnology, 2019; 19: 787-4790.
[2] Zhu A, et al. Phosphorylation amplified asymmetry of spiro[acridine-9,9'-xanthene] hosts for efficient blue and white thermal activated delay fluorescent diodes. Journal of Materials Chemistry C, 2023.